Omega, Breitling, and Heuer make an appearance — plus the Rolex Daytona, known as the holy grail among watch collectors

Rolex Daytona "Paul Newman," $85,000

Rolex Daytona "Paul Newman," $85,000

"All watch lovers have a list of grail watches, and this watch tops just about everyone's list. The Paul Newman Daytona is arguably the most desirable vintage chronograph on the planet, with its "exotic" dial that only came into favor once collectors noticed Mr. Newman himself wearing it in the 1970s." — Ben Clymer

Rolex Day-Date, $9,750

Rolex Day-Date, $9,750

"The Rolex Day-Date (aka the "President") is the quintessential watch of the 20th century, period. No watch in history is more lauded, more revered, or more copied by competitors, and this example is phenomenally beautiful, not to mention rare." — B.C.